Succinyl-disalicylic acid.



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RUDOLPH BERENDES AND JURGEN OALLSEN, or ELBERFELD, GERl\ IANY, ASSIGNORS To FARBENFABRIKEN VORM. FRIEDR. BAYER (la 00., OF ELBERFELD, GERMANY, A GORPl-' RATION OF GERMANY.

SUCCZNYL-DISALIGYLIC ACID.

No. erases.

Specification of Letters Patent.

Patented Dec. 31, 1907.

To all whom it may concern: o

Be it known that we, RUDOLPH Bnnsimns and Juneau CALLSEN, doctors of philosophy, chemists, citizens of the German Empire, residing at Elberield, Germany, Kingdom of Prussia, have invented new and. useful improvements in Suecinyl-Disalicylic Acid, of which the following is a specification.

Our invention relates to the preparation of the hitherto unknown succinyl disallcylic acid having the formula:

tvhich can be prepared by treating salicylic acid or its salts with the acid dihalogcnids of snccinic acid.

The succinyl-di salicylic acid is a valuable therapeutic compound. It is almost tasteless and non-irritant and is more easily split up and better absorbed than the known acidylized derivatives of salicylic acid frequently administered as substitutes for salicylic acid. It has also proved to be a stronger diapuorctic than these substances. it is to be prescribed or taken in similar doses as sodium salicylate or acetyl salicylic acid, an average dose being about one gram.

In order to illustrate our invention We give the following example, the parts being by weight: 155 parts of succinyl chlorid are slowly added to a solution of 276 parts of salicylic acid inIOO par-ts of benzene and 300 parts of dimethylanilin. The addition of the snccinyl chlorid is best carried out at a temperature of about 20 C. The mixture is allowed to stand for some hours. it is then poured into Water and an excess of HCl is added thereto. The succinyl-disalicylic acid separates on stirring tor. a short time as a solid body, its precipitation is accelerated by the addition of ligroin. it is filtered ofi, Washed with water and re crystallized from glacial acetic acidor alcohol. The new compound forms a crystalline powder'melting at about Nil-180 C. It is odorless and almost tasteless, soluble with difii'culty in cold alcohol and glacial acetic acid and scarcely soluble in Water. On boiling the succinyl-di-salicylic acid with water or with alkalies it is decomposed, succinic acid and salicylic acid being formed.

The following equation illustrates the reaction which takes place: I

un -cool coon on oooo mooos 1 The new succinyl salicylic acid possesses the property of forming salts With many metals, for example: the alkaline metals; the hydrogen of the'carboxyl groups being replaced by the metal. In this manner either neutral or acid salt-s may be obtained. The new acid may also form salts with organic bases, such as: liexsmethyl-entetramin lhcsc salts represent the usual addition products of 1 molecule of the acid and 1 or 2 molecules of the base. All these salts have substantially the same therapeutic eliect.

The process is carried out in an analogous manner on using instead of salicylic acid salts of salicylic acid; but in the case of salts there is no necessity of adding dimethylanilin. Furthermore succinyl chloridmay be replaced by succinyl bromid anddimethyl anilin by other bases such as diethyl anilin,

quinolin etc., capable of fixing the halogen hydrogeus. 1

Having now described our invention and in What mannerthe same is to be performed,

What We claim as new and desire to secure by Letters Patent is y The liereinalescribed new snccinyl-di-salicylic acid obtainable by the action of the acid dichlcrid of succinic acid upon salicylic acid, which in the acid form is a White crystalline powder melting at 17 8-18() (3.,soluble with diiiiculty in cold alcohol and glacial acetic.

acid, scarcely soluble in water and which by heating with caustic alkalies is decomposed into succinic acid and salicylic acid, forming salts with ,bases which retain the valuable therapeutic properties exhibited by the acid,

substantially as hereinbefore described.

' In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.

RUDOLPH BERENDES. e 5. JURGEN oALLsEN. [Le] A Witnesses:

OTTO Komc, .OSKAR KLUG. 

